Compounds derived from halonitroanthraquinones



COMPOUNDS DERIVED FROM HALONITRO- HR Q INQNE William L. Mosby, mi rnmfii, as William L. Berry,

Neshanic, NJ., assignors to American Cyanamid Company, New York, N.Y., a corporation of Maine No Drawing. Filed Oct. 12, 1959, Ser. No. 845,620 3 Claims. (Cl. 260-272) This invention relates to new polycyclic, heterocyclic compounds usable as vat dyes or pigments. More specifically, it relates to the new compounds of the structure @C O N I! N C O in which the carbonyls are linked with adjoining carbons of the ring A.

We have found that when Z-aminopyridines are heated with an ortho-nitrohaloanthraquinone, the resulting prodnet is a pyridoimidazoloanthraquinone of the unique structure given above. We have further found that the compounds of our invention are excellent orange pigments and vat dyes.

The halonitroanthraquinones used as the starting materials for our invention are readily available by the peracetic acid oxidation of aminohaloanthraquinones which we have reported elsewhere (Tetrahedron, 5, 93 (1959)). As convenient starting materials, depending on whether a 1,2 or 2,3 configuration is desired, we prefer to use 1-chloro-2-nitroanthraquinone prepared from l-chloro-Z-aminoanthraquinone or 2-bromo-3-nitroanthraquinone prepared from 2-amino-3-brornoanthraquinone. Starting with l-chloro-2-nitroanthraquinone one obtains the vat dye of the structure while 2-bromo-3-nitroanthraquinone produces the linear dye of the structure Both of these compounds of our invention are orange in color and dye cotton an orange shade from red vats.

They are furthermore usable as orange coloring mate- 7 rials for resins, as well as for hydrocarbons such as gasoline.

'is then milled with 50 2,938,904 PatentedMay 31, 1960 amples in which parts-are by .weight unless otherwise specified.

Example 1 N H N Example 2 i A mixture of 16.6 parts of 2-bromo-3-nitroanthraquinone, 14.1 parts of Z-aminopyridine and 0.4 part of cupric acetate in parts by volume of glycol diacetate is stirred under reflux until the reaction is substantially complete. The cooled mixture is filtered and the brownish yellow solid is sublimed in a vacuum. The orange product can be recrystallized from trichlorobenzene. It dyes cotton an orange shade from a red vat.

Example 3 Five parts of the product of Example 1 is ground to a fine powder and added to 100 parts of polyvinylchloride being milled on a 3-roll mill. The polyvinylchloride parts of di-2-ethylhexylphthala-te, 2 parts of barium cadmium laurate, and one part of a triarylphosphite. The composition is then molded in a standard way giving a sheet of polyvinylchloride having an orange color.

We claim:

1. A compound of the structure in which the carbonyls are linked with adjoining carbons of the ring A. 

1. A COMPOUND OF THE STRUCTURE 